# US 9,040,173 B2 · Triphenylene-based compounds and organic electroluminescent device comprising same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,173 B2 - Document ID: US9040173B2 - Status: Granted - Kind: B2 - Application number: 13/520,100 - Filed: 2010-12-29 - Published: 2013-01-10 - Granted: 2015-05-26 - Earliest claimed: 2009-12-30 - Assignees: Doosan Corporation - Applicants: Jin-Seok Hong; Chang-Ju Shin; Tae-Hyung Kim; Kyoung-Soo Kim - Inventors: Jin-Seok Hong; Chang-Ju Shin; Tae-Hyung Kim; Kyoung-Soo Kim - Web page: https://patentgrep.com/patent/US9040173B2 ## CPC - C09K 11/06: containing organic luminescent materials - H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} - C09K 2211/1007: Non-condensed systems - C09K 2211/1011: Condensed systems - C09K 2211/1029: containing one nitrogen atom as the heteroatom - C09K 2211/1033: with oxygen - C09K 2211/1037: with sulfur - C09K 2211/1059: containing three nitrogen atoms as heteroatoms - C09K 2211/1092: containing sulfur as the only heteroatom - H10K 50/11: characterised by the electroluminescent [EL] layers - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES ## Abstract The present invention relates to a triphenylene-based compound represented by the following Formula 1 and an organic electroluminescent device including the same, and the compound of the present invention has excellent hole injection and/or transporting ability, electron transporting ability, and/or light emitting ability, and particularly, green and red light emitting ability, and thus in an organic electroluminescent device containing the same as a light emitting host material, characteristics such as luminous efficiency, luminance, thermal stability, driving voltage, service life and the like may be improved. In the formula, each of A, L, X and R1 to R19 is the same as those as defined in Detailed Description. ## Claims ### Claim 1 A compound represented by the following Formula 1: in the formula, A means an N-containing 6- to 8-membered heterocycle; X is selected from the group consisting of —(CR20R21)n-, —(SiR22R23)m-, —NR24—, —O— and —S—, and n and m are each independently an integer of 1 to 3; R1 to R24 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 40 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylalkyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, a substituted or unsubstituted C1 to C40 haloalkyl, or cyano, and R1 to R23 may be bonded with a group adjacent to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring; and L is a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 60 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylalkyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, or a substituted or unsubstituted C1 to C40 haloalkyl. ### Claim 2 (depends on 1) The compound as claimed in claim 1, wherein the compound represented by Formula 1 is a compound represented by the following Formula 1a, 1b or 1c: in the formula, each of A, X and R1 to R19 is the same as those as defined in claim 1, R25 to R28 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 40 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylalkyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylakylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, a substituted or unsubstituted C1 to C40 haloalkyl, or cyano, and R25 to R28 may be bonded with a group adjacent to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring. ### Claim 3 (depends on 1) The compound as claimed in claim 1, wherein the compound represented by Formula 1 is a compound represented by the following Formula 1d: in the formula, each of A, X and R1 to R19 is the same as those as defined in claim 1, at least one of a plurality of Z's is a nitrogen atom and the rest thereof are a carbon atom, wherein if Z is carbon atom, Z is unsubstituted or substituted with deuterium, a halogen, a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 40 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylalkyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, a substituted or unsubstituted C1 to C40 haloalkyl, or cyano, and the substituent groups may be bonded with a group adjacent to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring. ### Claim 4 An organic electroluminescent device comprising: an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by the following Formula 1; in the formula, A means an N-containing 6- to 8-membered heterocycle; X is selected from the group consisting of —(CR20R21)n-, —(SiR22R23)m-, —NR24—, —O— and —S—, and n and m are each independently an integer of 1 to 3; R1 to R24 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 40 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylakyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, a substituted or unsubstituted C1 to C40 haloalkyl, or cyano, and R1 to R23 may be bonded with a group adjacent to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring; and L is a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 60 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylakyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, or a substituted or unsubstituted C1 to C40 haloalkyl. ### Claim 5 (depends on 4) The organic electroluminescent device as claimed in claim 4, wherein the organic layer is selected from the group consisting of a light emitting layer, an electron transporting layer, a hole injection layer and a hole transporting layer. ### Claim 6 (depends on 4) The organic electroluminescent device as claimed in claim 4, wherein the compound is a phosphorescent host material or a fluorescent host material. ### Claim 7 (depends on 4) The organic electroluminescent device as claimed in claim 4, wherein the compound represented by Formula 1 is a compound represented by the following Formula 1a, 1b or 1c: in the formula, each of A, X and R1 to R19 is the same as those as defined in claim 4, R25 to R28 are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 40 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylamino wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, a substituted or unsubstituted C1 to C40 haloalkyl, or cyano, and R25 to R28 may be bonded with a group adjacent to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring. ### Claim 8 (depends on 4) The organic electroluminescent device as claimed in claim 4, wherein the compound represented by Formula 1 is a compound represented by the following Formula 1d: in the formula, each of A, X and R1 to R19 is the same as those as defined in claim 4, at least one of a plurality of Z's is a nitrogen atom and the rest thereof are a carbon atom, wherein if Z is carbon atom, Z is unsubstituted or substituted with deuterium, a halogen, a substituted or unsubstituted C1 to C40 alkyl, a substituted or unsubstituted heterocycle having 3 to 40 nuclear atoms, a substituted or unsubstituted C1 to C40 alkoxy, a substituted or unsubstituted aromatic hydrocarbon having 6 to 40 nuclear atoms, a substituted or unsubstituted C6 to C40 aryloxy, a substituted or unsubstituted arylalkyl wherein aryl is C7 to C40 aryl and alkyl is C1 to C40 alkyl, a substituted or unsubstituted C2 to C40 alkenyl, a substituted or unsubstituted C1 to C40 alkylamino, a substituted or unsubstituted C6 to C40 arylamino, a substituted or unsubstituted arylalkylamino wherein aryl is C7 to C40 aryl and alkylamino is C1 to C40 alkylamino, a substituted or unsubstituted C3 to C20 alkylsilyl, a substituted or unsubstituted C8 to C40 arylsilyl, a substituted or unsubstituted C7 to C40 ketoaryl, a substituted or unsubstituted C1 to C40 haloalkyl, or cyano, and the substituent groups may be bonded with a group adjacent to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring.